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Benzene-1,2-dithiol

Benzene-1,2-dithiol is the organosulfur compound with the formula CH(SH). This colourless viscous liquid consists of a benzene ring with a pair of adjacent thiol groups. The conjugate base of this diprotic compound serves as chelating agent in coordination chemistry and a building block for the synthesis of other organosulfur compounds.

Synthesis

The compound is prepared by ortho-lithiation of benzenethiol using butyl lithium (BuLi) followed by sulfidation: :CHSH + 2 BuLi → CHSLi-2-Li + 2 BuH :CHSLi-2-Li + S → CH(SLi) :CH(SLi) + 2 HCl → CH(SH) + 2 LiCl

The compound was first prepared from 2-aminobenzenethiol via diazotization. Alternatively, it forms from 1,2-dibromobenzene.

Reactions

Oxidation mainly affords the polymeric disulfide. Reaction with metal dihalides and metal oxides gives the dithiolate complexes of the formula LM(SCH) where LM represents a variety of metal centers, e.g. (CH)Ti. Ketones and aldehydes condense to give the heterocycles called dithianes: :CH(SH) + RR’CO → CH(S)CRR’ + HO

References

References

  1. Karlin, K. D.; Stiefel, E. I., Eds. “Progress in Inorganic Chemistry, Dithiolene Chemistry: Synthesis, Properties, and Applications” Wiley-Interscience: New York, 2003. {{ISBN. 0-471-37829-1
  2. D. M. Giolando. (1992). "An efficient one-pot synthesis of 1,2-benzenedithiol from benzenethiol". [[Synthesis (journal).
  3. P. C. Guha. (1925). "Dithiocatechol". J. Indian Chem. Soc..
  4. Aldo Ferretti. "1,2-Dimercaptobenzene".
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